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Method for making functionalized polymer

a functionalized polymer and polymer technology, applied in the field of functionalized polymer making, can solve the problems of heat loss of energy transmitted to this section of the polymer (and the vulcanizate in which such polymer is incorporated)

Active Publication Date: 2014-03-25
BRIDGESTONE CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent describes a method for creating a polymer with terminal functionality by reacting a cyclic compound with a silicon atom. This polymer can be used to create compositions with particulate fillers, such as carbon black or silica. The resulting compositions have improved properties such as increased strength or reduced rolling resistance. The patent also describes a method for creating a random interpolymer with mer units derived from each type of constituent monomer. The polymer can have various functional groups attached to it, such as hydrocarbyl groups or heteroatoms. The patent also provides definitions for various terms used in the text.

Problems solved by technology

These considerations are, to a great extent, competing and somewhat contradictory: treads made from compositions designed to provide good road traction usually exhibit increased rolling resistance and vice versa.
The section of a polymer chain from the site of the last crosslink to an end of the polymer chain is a major source of hysteretic losses; this free end is not tied to the macro-molecular network and thus cannot be involved in an efficient elastic recovery process and, as a result, energy transmitted to this section of the polymer (and vulcanizate in which such polymer is incorporated) is lost as heat.

Method used

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  • Method for making functionalized polymer
  • Method for making functionalized polymer

Examples

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examples

[0077]In the examples, dried glass vessels previously sealed with extracted septum liners and perforated crown caps under a positive N2 purge were used for all preparations.

[0078]The following materials were obtained from a laboratory storeroom or synthesized: butadiene solution (in hexane), styrene solution (33.5% in hexane), hexane, n-butyllithium (1.6 M in hexane), 2,2-bis(2′-tetrahydrofuryl)propane (1.6 M solution in hexane, stored over CaH2), butylated hydroxytoluene (BHT) solution in hexane, and 4-dimethylaminophenyl-1,3-dithiane (DMAPDT).

[0079]Commercially available reagents and starting materials included the following, all of which were acquired from Gelest Inc. (Morrisville, Pa.) and used without further purification unless otherwise noted in a specific example: di-t-butylchlorosilane, phenylmethyl-chlorosilane, dimethylaminoethoxysilane, methyldimethoxysilane, methyldiethoxysilane, phenyldiethoxysilane (95% purity), phenylhydrocyclosiloxanes (95% purity, “PHCS”), methylhy...

examples 1-5

[0080]To a N2-purged reactor equipped with a stirrer was added 1.66 kg hexane, 0.45 kg styrene solution, and 2.84 kg butadiene solution (21.1% by wt. in hexane). The reactor was charged with 3.81 mL n-butyllithium, followed by 1.2 mL 2,2-bis(2′-tetrahydrofuryl)propane solution. The reactor jacket was heated to 50° C. and, after ˜34 minutes, the batch temperature peaked at −68° C. This control polymer is identified as sample 1 in Table 1 below.

[0081]After being charged with the same amounts of solvent and reactants, the reactor was charged 3.90 mL n-butyllithium, followed by 1.2 mL 2,2-bis(2′-tetrahydrofuryl)propane solution. The reactor jacket was heated to 50° C. and, after ˜33 minutes, the batch temperature peaked at −68° C. After ˜30 minutes, a 4.12 M solution of 1.6 mL TMCTS in 10 mL hexane was charged to the reactor and stirred at 50° C. for an additional ˜30 minutes. Four portions of the polymer cement were dropped into dried glass bottles. One bottle (sample 2) was set aside ...

examples 6-9

[0084]To a N2-purged reactor equipped with a stirrer was added 1.60 kg hexane, 0.45 kg styrene solution, and 2.89 kg butadiene solution (20.7% by wt. in hexane). The reactor was charged with 3.98 mL n-butyllithium, followed by 1.2 mL 2,2-bis(2′-tetrahydrofuryl)propane solution. The reactor jacket was heated to 50° C. and, after ˜31 minutes, the batch temperature peaked at ˜65° C.

[0085]After an additional 30 minutes at 50° C., portions of the polymer cement were dropped into dried glass bottles. One was terminated with isopropanol (designated sample 6 below), while the other three were reacted with a cyclic siloxane:[0086]sample 7—4.8 M MHCS,[0087]sample 8—2.3 M PHCS, and[0088]sample 9—3.3 M TECTS.

In each of samples 7-9, cyclic siloxane was added so as to provide a 1:1 ratio of initiator-to-siloxane. Each of the bottles were kept in a 50° C. water bath for ˜30 minutes.

[0089]Each of the four polymer cements was dropped separately into isopropanol containing BHT and then drum dried. Th...

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Abstract

A macromolecule includes at least one polymer chain and terminal functionality. The terminal functionality includes a ring-opened radical of a cyclosilazane or cyclic hydrosiloxane. The polymer can include unsaturated mer units and can be provided via anionic polymerization techniques. The macromolecule can be used as a component of a composition that also includes particulate fillers, with the composition being useful for the production of vulcanizates.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This application claims the benefit of U.S. provisional patent appl. No. 61 / 481,313, filed May 2, 2011, the entire disclosure of which is incorporated herein by reference.BACKGROUND INFORMATION[0002]Rubber goods such as tire treads often are made from elastomeric compositions that contain one or more reinforcing materials such as, for example, particulate carbon black and silica; see, e.g., The Vanderbilt Rubber Handbook, 13th ed. (1990), pp. 603-04.[0003]Good traction and resistance to abrasion are primary considerations for tire treads; however, motor vehicle fuel efficiency concerns argue for a minimization in their rolling resistance, which correlates with a reduction in hysteresis and heat build-up during operation of the tire. These considerations are, to a great extent, competing and somewhat contradictory: treads made from compositions designed to provide good road traction usually exhibit increased rolling resistance and vice vers...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C08C19/25
CPCC08C19/44C08F36/04C08F212/08C08F4/48C08F4/58
Inventor YAN, YUAN-YONG
Owner BRIDGESTONE CORP
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